C2-HSL, N-Acetyl-L-hoMoserine lactone synthesis

4synthesis methods

Product Name:C2-HSL, N-Acetyl-L-hoMoserine lactone
CAS Number:51524-71-1
Molecular formula:C6H9NO3
Molecular Weight:143.14

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2(3H)-Furanone, 3-aminodihydro-, (3S)-, 2,2,2-trifluoroacetate (1:1)

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51524-71-1
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Yield:51524-71-1 80%

Reaction Conditions:

with sodium hydrogencarbonate in water at 0 - 20; for 0.583333 h;

Steps:

(S)-N-(2-oxotetrahydrofuran-3-yl)acetamide(2)

To a cold (0 °C) solution of 13(890 mg, 4.14 mmol) in 14 mL water added Ac₂O (586 μL, 6.2 mmol)followed by NaHCO₃ (1.04 gm, 12.42 mmol) and the mixture was stirred at 0 °C for 5 min and the ice bath was removed. The mixture was then stirred for 30 min at rt. Purification by silica gel flash column chromatography (EtOH: DCM - 4 : 96) yielded the desired product as a white solid (473 mg, 3.3 mmol,80%) (TLC: MeOH : DCM (15:85)- R_f = 0.35). IR (NaCl, 10 mM in CHCl₃):3462, 3428, 3342, 3027, 3010, 2953, 2917, 2884, 1782, 1682, 1512, 1380, 1292,1265, 1173, 1159, 1015, 951, 841, 734, 654, 596 cm^-1; H NMR (400 MHz, CDCl₃)δ ppm: 6.03 (bs, 1H), 4.58-4.52 (m, 1H), 4.47 (t, J = 8.9 Hz, 1H), 4.31-4.25 (m, 1H), 2.89-2.83 (m, 1H), 2.22-2.08(m, 1H), 2.06 (s, 3H); C NMR (100 MHz, CDCl₃) δ ppm: 175.8, 170.8, 66.0, 48.9, 29.7, 22.7; HRMSm/z Calcd for C₆H₉NO₃Na 166.0480,Found 166.0484.

References:

Tumminakatti, Shama;Khatri, Bhavesh;Krishnamurti, Vinayak;Athavale, Vishikh;Prabhakaran, Erode N. [Tetrahedron Letters,2015,vol. 56,# 42,p. 5771 - 5775] Location in patent:supporting information

672-15-1 Synthesis